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First Night Festivities at the Family Y

Dennis the Train Man will be set up in the Y's Upper Gym from 5 to 7 pm on New Year's Eve.

First Night Westport/Weston is a community-wide celebration of New Year’s Eve through the arts.  Over thirty events featuring performances for children, teens and adults are presented throughout downtown Westport.

One of the primary destinations is our Family Y, from the horse-drawn carriage rides that begin near the front steps of the Bedford Building to all the attractions all evening long inside our doors.

First Night begins Dec. 31 at 4pm and ends at 10:30pm . Please click here to view the complete schedule.

Buttons are $10 from now until December 14th.  On December 15th the price goes up to $15. Children two and under are always free.  The website lists the places that are selling the buttons.  They are a great holiday gift!

First Night Festivities at the Westport Weston Family Y


Black light puppet show is the ultimate puppet experience. Big mouth, furry hand puppets glow in the dark under the black lights. Scene setters, black light reactive bubbles and props are used to enhance the experience. Children are encouraged to wear white so they will glow too! Ultra VioletBlack light puppet shows are geared for children from 3-10 years old. UVP will have your little ones laughing, earning, dancing and delighting in the fun, interactive and unique show! Our educational puppet shows focus on educating children through the art of puppetry. Children will sing along, get up and dance and learn important lessons about friendship, good character, not bullying, cultural diversity, acceptance, recycling, having a healthy body image and much more!

8 – 8:45pm, 9 – 9:45pm

Get ready for the thrill of your life.   Here comes the Magic Genie.  He has traveled around the world and has developed a presentation of magic that is astonishing, unbelievable and incredible.  And, he plans on teaching you how to do some of it!!!


5 – 7pm
The very popular Dennis the Train Man returns with his collection of trains and tales to tell about them.  Included this year is Amtrak, Thomas the Tank Train, the New York City Subway and the very special Harry Potter Hogwarth’s Express!!!

5 – 10pm

For an additional $3.00 you can literally be transformed. Amazing Face Art is truly amazing and kids and adults will be thrilled by their artistic creations. Amazing Face Art provides face and body painting, airbrush art, for any event in Connecticut and surrounding areas.

It’s your children’s skin!! They only use the safest and highest quality face paints in the market. They are hypoallergenic, non toxic and FDA approved. Easily washes off with soap and water

6 -10pm
Caricaturist Mike Valentine, will capture you with his funny but flattering drawings


4 – 6pm
Bob Lasprogato & Uptown Jazz play a mixture of New Orleans jazz and standard tunes by composers such as George Gershwin, Cole Porter, Duke Ellington and the like. Bob has been drumming since age 14 and led his first band while still in high school. He has performed all over the United States and Europe with jazz greats as Ellis Larkins, Ken Peplowski, and Brian Torff.  The musicians joining Bob are Paul Boehmke, sax, clarinet and vocals. Gim Burton, a long time member of the Bearcats Jazz Band will be playing guitar & banjo, and Phil Bowler will be performing on string bass. Phil has worked with such jazz luminaries as Wynton Marsalis, Rahsaan Roland Kirk and Max Roach.


6:15 – 8:15pm
Washboard Slim and the Blue Lights are bringing jug band music into the 21st century. The music the Bluelights perform is at the very root of traditional American popular music. A typical Bluelights performance might include original music, early jazz, blues, swing, standards, jug band, gospel, pop music from the turn of the century and roots rock ‘n’ roll. Starting in 1986, they continue to perform at festivals, concerts and clubs throughout North America.

Washboard Slim and the Bluelights are among the performers at the Y on First Night.


4 – 9pm

Horse drawn carriage rides